Every summer the same debate comes out to play. How short is too short for shorts??? Well after doing some research on the famous denim cut off shorts I've drawn to the conclusion that it's not so much a question of what is too short for summer shorts, there's a lot more behind it than that. Like what body type do you have? What kind of shoes are you pairing with these shorts? What kind of top are you wearing? Where are you going? Etc… After evaluating all these aspects then you may come to a conclusion of what is too short for you and the occasion.
I have heard many people say that if the pockets of your shorts are showing then they too short well if we look closely at the pictures of Halle Berry we can clearly see her pockets coming out of her shorts, but the shorts are of an appropriate length for her body type and especially the way she has paired them with both a baseball cap and a basic t-shirt. Maybe if she had paired those shorts with a cropped top and a pair of heels they could've been inappropriate. But by keeping her look casual she has kept her look clean and classic.
Here's an example of 2 different body types wearing similar shorts, as you can see with Ciara having a more curvaceous body her shorts appear to be smaller and be a lil more sexual in look. But she has balanced it out by pairing it with a loose fitted tank and fun coloured heels, also by not letting any other body part show she lets her legs take the center of attention. While on Gisele the shorts seem more a bit more chic since they aren't as fitted on her due to her different body shape, she has also paired her shorts with a loose fitted tank and heels. Looking at both looks side by side makes us realize that it's not always the shorts but the body that's wearing them.
Now I'm sure we can all agree that if it looks like you're wearing diapers when you put on your shorts then no matter where you're going, what your body type is, or what you pair them with it won't be a good look. This look is just a fail in general.
So I think in all as long as you keep your look casual only letting your legs do the show stopping while wearing short shorts, the appropriate length is to your comfort level. Remembering that diaper shorts are not cool and if I can see your underwear that you're wearing under your shorts then it probably should only be worn on beach or in the privacy of your own home.
Via: How Short is too Short for Short Shorts?